Abstract
A bioassay-guided fractionation and chemical investigation of Amaryllis belladonna Steud. bulbs resulted in the isolation and identification of the new crinane alkaloid 1,4-dihydroxy-3-methoxy powellan (1), along with the 3 known crinane alkaloids 2-4 and the two lycorane alkaloids 5-6. The structures were elucidated by interpretation of combined HR-ESIMS, CD and 2D NMR spectroscopic data. Among these isolated compounds the lycorane-type alkaloid acetylcaranine (5) exhibited strong antiplasmodial activity, while compounds 3 and 4 were moderately active, and compounds 1 and 6 were inactive.
Keywords:
Amaryllis belladonna; Antiplasmodial; Bioassay-guided; Crinane; Lycorine.
Copyright © 2017 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkaloids / chemistry*
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Alkaloids / isolation & purification
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Alkaloids / pharmacology
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Amaryllidaceae Alkaloids / chemistry*
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Amaryllidaceae Alkaloids / isolation & purification
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Amaryllidaceae Alkaloids / pharmacology
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Antimalarials / chemistry*
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Antimalarials / isolation & purification
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Antimalarials / pharmacology
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Asparagales / chemistry*
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Asparagales / metabolism
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Circular Dichroism
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Humans
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Magnetic Resonance Spectroscopy
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Molecular Conformation
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Plant Extracts / chemistry
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Plant Roots / chemistry
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Plant Roots / metabolism
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Plasmodium falciparum / drug effects
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Spectrometry, Mass, Electrospray Ionization
Substances
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1,4-dihydroxy-3-methoxypowellan
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Alkaloids
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Amaryllidaceae Alkaloids
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Antimalarials
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Plant Extracts